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#1 2011-08-09 02:12:59

orgopete
Administrator

Deduce 3-methylene-1-cyclohexene from UV and Rxn

Compound A is a clear, colorless liquid with a molecular formula of C7H10. Upon treatment of A with H2 gas in the presence of Pd on carbon, a single product B (C7H14) is obtained. Compound A has a λmax at 232 nm in its UV spectrum but will not react with any dienophile in a Diels-Alder fashion. Provide a structure for Compound A, and explain how you arrived at your decision.

The UV indicates it is a conjugated diene, but the Diels Alder reaction fails so this tells us it cannot react. Also, the reduction product has a ring. If it were a chain, product B would be C7H16. There are a couple of possibilities. Let me draw one.

     http://www.curvedarrow.com/chem/ZZ1E7665E2.jpg

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